A Rotational Study of 2‐tert‐Butylphenol and Its 1 : 1 Argon Complex

Abstract

AbstractThe chirped‐pulse Fourier Transform microwave spectrum of 2‐tert‐butylphenol, an industrial intermediate for the production of antioxidants, has been investigated in the 2–8 GHz frequency range. The spectral analysis has allowed obtaining precise structural information on the most stable conformer and its complex with argon. The conformation of the monomer reveals that the hydroxyl group is coplanar with the ring but points in the opposite direction to the tert‐butyl group, reducing steric interactions. In the tert‐butyl group one methyl group is coplanar and the other two are symmetrically staggered respect to the ring. The complex shows the rare gas sitting above the aromatic ring. Interestingly, neither the monomer nor the complex exhibit large‐amplitude hydroxyl torsion motions, previously observed in 2,6‐disubstituted phenols such as 2,6‐di‐tert‐butylphenol or propofol. The experimental results are supported by computational calculations, validating the molecular structure. Additionally, symmetry‐adapted perturbation theory has allowed determining the van der Waals intermolecular interaction energy of the complex.